Dynamic Kinetic Asymmetric Domino Oxa-Michael/Carbocyclization by Combination of Transition-Metal and Amine Catalysis: Catalytic Enantioselective Synthesis of Dihydrofurans

被引：65

作者：

Lin, Shuangzheng ^{[1
]}

Zhao, Gui-Ling ^{[1
,2
]}

Deiana, Luca ^{[1
,2
]}

Sun, Junliang ^{[2
,3
]}

Zhang, Qiong ^{[4
]}

Leijonmarck, Hans ^{[1
,2
]}

Cordova, Armando ^{[1
,2
,5
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[2] Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, Arrhenius Lab, S-10691 Stockholm, Sweden

[3] Stockholm Univ, Dept Struct Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[4] Royal Inst Technol, Dept Theoret Chem, Sch Biotechnol, S-10691 Stockholm, Sweden

[5] Mid Sweden Univ, Dept Nat Sci Engn & Math, S-85170 Sundsvall, Sweden

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 47期

关键词：

asymmetric catalysis; co-catalysis; domino reactions; furans; palladium; ONE-POT SYNTHESIS; ALLYLIC ALKYLATION; FORMAL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CASCADE CATALYSIS; ENOL ETHERS; ALDEHYDES; PALLADIUM; CYCLIZATIONS; IMINIUM;

D O I：

10.1002/chem.201001992

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Into the pot: A one-pot highly chemo- and enantioselective catalytic domino oxa-Michael/carbocyclization between α,β-unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition-metal and amine catalysis to afford functionalized dihydrofurans in good to high yields and up to 99.5:0.5 e.r. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：13930 / 13934

页数：5

共 118 条

[1] Domino hydroformylation/enantioselective cross-aldol addition [J].

Abillard, Olivier ;

Breit, Bernhard .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1891-1895

[2]

Anastas P.T., 2000, Green Chemistry: Theory and Practice, P135, DOI DOI 10.1021/OP000054T

[3]

[Anonymous], 2009, ANGEW CHEM INT EDIT

[4]

[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[5]

[Anonymous], 2008, ANGEW CHEM

[6] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[7]

AYERES DC, 1990, LIGNANS CHEM BIOL CL

[8]

BAANDAU S, 2006, ANGEW CHEM, V118, P4411

[9] Element-element additions to unsaturated carbon-carbon bonds catalyzed by transition metal complexes [J].

Beletskaya, Irina ;

Moberg, Christina .

CHEMICAL REVIEWS, 2006, 106 (06) :2320-2354

[10]

Beller M., 2004, TRANSITION METALS OR

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